Friedel-Crafts reaction of activated benzene rings with captodative and electron-deficient alkenes. A one-step synthesis of the natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate

被引：19

作者：

Aguilar, R ^{[1
]}

Benavides, A ^{[1
]}

Tamariz, J ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Mexico City 11340, DF, Mexico

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 15期

关键词：

Friedel-Crafts; captodative olefins; methyl 3-(2,4,5-trimethoxyphenyl)propionate;

D O I：

10.1081/SCC-200026193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic aromatic substitution of activated benzenes with the captodative olefin 1-acetylvinyl-1-p-nitrobenzoate (9), and with the electron-deficient alkenes methyl acrylate (8a), methylvinylketone (8b), and acrolein (8c) were evaluated under Lewis acid catalysis. Olefin 9 proved to be much more reactive than alkenes 8a-8c. We also describe a one-step synthesis of the antifungal and larvicidal natural product methyl 3-(2,4,5-trimethoxyphenyl)propionate (6), by reaction of 1,2,4-trimethoxybenzene with 8a under microwave irradiation.

引用

页码：2719 / 2735

页数：17

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